Vinclozolin
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MedKoo CAT#: 461406

CAS#: 50471-44-8

Description: Vinclozolin is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards.

Chemical Structure

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Vinclozolin
CAS# 50471-44-8
Instruction

Theoretical Analysis

MedKoo Cat#: 461406
Name: Vinclozolin
CAS#: 50471-44-8
Chemical Formula: C12H9Cl2NO3
Exact Mass: 285.00
Molecular Weight: 286.100
Elemental Analysis: C, 50.38; H, 3.17; Cl, 24.78; N, 4.90; O, 16.78

Price and Availability

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250mg USD 210
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Synonym: Vinclozolin; Ornalin; Ronilan; Vorlan;

IUPAC/Chemical Name: 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione

InChi Key: FSCWZHGZWWDELK-UHFFFAOYSA-N

InChi Code: InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3

SMILES Code: O=C(N1C2=CC(Cl)=CC(Cl)=C2)OC(C)(C=C)C1=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 286.10 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Salleh N, Giribabu N, Feng AO, Myint K. Bisphenol A, Dichlorodiphenyltrichloroethane (DDT) and Vinclozolin Affect ex-vivo Uterine Contraction in Rats via Uterotonin (Prostaglandin F2α, Acetylcholine and Oxytocin) Related Pathways. Int J Med Sci. 2015 Oct 27;12(11):914-25. doi: 10.7150/ijms.11957. eCollection 2015. PubMed PMID: 26640411; PubMed Central PMCID: PMC4643082.

2: Wu YH, Wu TM, Hong CY, Wang YS, Yen JH. Screening differentially expressed genes in an amphipod (Hyalella azteca) exposed to fungicide vinclozolin by suppression subtractive hybridization. J Environ Sci Health B. 2014;49(11):856-63. doi: 10.1080/03601234.2014.938556. PubMed PMID: 25190560.

3: Aquilino M, Sánchez-Argüello P, Martínez-Guitarte JL. Vinclozolin alters the expression of hormonal and stress genes in the midge Chironomus riparius. Aquat Toxicol. 2016 May;174:179-87. doi: 10.1016/j.aquatox.2016.03.001. Epub 2016 Mar 4. PubMed PMID: 26966872.

4: de Oca FG, López-González Mde L, Escobar-Wilches DC, Chavira-Ramírez R, Sierra-Santoyo A. Vinclozolin modulates hepatic cytochrome P450 isoforms during pregnancy. Reprod Toxicol. 2015 Jun;53:119-26. doi: 10.1016/j.reprotox.2015.04.010. Epub 2015 Apr 28. PubMed PMID: 25929820.

5: Gillette R, Miller-Crews I, Nilsson EE, Skinner MK, Gore AC, Crews D. Sexually dimorphic effects of ancestral exposure to vinclozolin on stress reactivity in rats. Endocrinology. 2014 Oct;155(10):3853-66. doi: 10.1210/en.2014-1253. Epub 2014 Jul 22. PubMed PMID: 25051444; PubMed Central PMCID: PMC4164929.

6: Auxietre TA, Dumontier MF, Balguy I, Frapart Y, Canivenc-Lavier MC, Berges R, Boudalia S, Auger J, Corvol MT, Savouret JF. Sub-NOAEL amounts of vinclozolin and xenoestrogens target rat chondrogenesis in vivo. Biochimie. 2014 Apr;99:169-77. doi: 10.1016/j.biochi.2013.12.001. Epub 2013 Dec 12. PubMed PMID: 24333988.

7: Lor Y, Revak A, Weigand J, Hicks E, Howard DR, King-Heiden TC. Juvenile exposure to vinclozolin shifts sex ratios and impairs reproductive capacity of zebrafish. Reprod Toxicol. 2015 Dec;58:111-8. doi: 10.1016/j.reprotox.2015.09.003. Epub 2015 Sep 28. PubMed PMID: 26423773.

8: van Ravenzwaay B, Kolle SN, Ramirez T, Kamp HG. Vinclozolin: a case study on the identification of endocrine active substances in the past and a future perspective. Toxicol Lett. 2013 Dec 16;223(3):271-9. doi: 10.1016/j.toxlet.2013.03.029. Epub 2013 Apr 1. PubMed PMID: 23558297.

9: Paoloni-Giacobino A. Epigenetic effects of methoxychlor and vinclozolin on male gametes. Vitam Horm. 2014;94:211-27. doi: 10.1016/B978-0-12-800095-3.00008-0. Review. PubMed PMID: 24388192.

10: Schuster A, Skinner MK, Yan W. Ancestral vinclozolin exposure alters the epigenetic transgenerational inheritance of sperm small noncoding RNAs. Environ Epigenet. 2016;2(1). pii: dvw001. Epub 2016 Mar 9. Erratum in: Environ Epigenet. 2016 Apr 14;2(2):dvw004. PubMed PMID: 27390623; PubMed Central PMCID: PMC4933025.

11: Knet M, Wartalski K, Hoja-Lukowicz D, Tabarowski Z, Slomczynska M, Duda M. Analysis of porcine granulosa cell death signaling pathways induced by vinclozolin. Theriogenology. 2015 Oct 1;84(6):927-39. doi: 10.1016/j.theriogenology.2015.05.028. Epub 2015 Jun 6. PubMed PMID: 26141531.

12: Cho S, Kim J, Lee S, Kim TH. Vinclozolin: 3-(3,5-di-chloro-phen-yl)-5-ethenyl-5-methyl-1,3-oxazolidine-2,4-dione. Acta Crystallogr Sect E Struct Rep Online. 2014 Jun 7;70(Pt 7):o754. doi: 10.1107/S1600536814012781. eCollection 2014 Jul 1. PubMed PMID: 25161548; PubMed Central PMCID: PMC4120555.

13: Alvarado-Flores J, Rico-Martínez R, Adabache-Ortíz A, Silva-Briano M. Morphological alterations in the freshwater rotifer Brachionus calyciflorus Pallas 1766 (Rotifera: Monogononta) caused by vinclozolin chronic exposure. Ecotoxicology. 2015 May;24(4):915-25. doi: 10.1007/s10646-015-1434-8. Epub 2015 Mar 1. PubMed PMID: 25725815.

14: Liu H, Liu D, Shen Z, Sun M, Zhou Z, Wang P. Chiral separation and enantioselective degradation of vinclozolin in soils. Chirality. 2014 Mar;26(3):155-9. doi: 10.1002/chir.22284. Epub 2014 Feb 4. PubMed PMID: 24497202.

15: Taguchi YH. Identification of aberrant gene expression associated with aberrant promoter methylation in primordial germ cells between E13 and E16 rat F3 generation vinclozolin lineage. BMC Bioinformatics. 2015;16 Suppl 18:S16. doi: 10.1186/1471-2105-16-S18-S16. Epub 2015 Dec 9. PubMed PMID: 26677731; PubMed Central PMCID: PMC4682393.

16: Knet M, Tabarowski Z, Slomczynska M, Duda M. The effects of the environmental antiandrogen vinclozolin on the induction of granulosa cell apoptosis during follicular atresia in pigs. Theriogenology. 2014 Jun;81(9):1239-47. doi: 10.1016/j.theriogenology.2014.02.005. Epub 2014 Feb 13. PubMed PMID: 24636578.

17: Christen V, Crettaz P, Fent K. Additive and synergistic antiandrogenic activities of mixtures of azol fungicides and vinclozolin. Toxicol Appl Pharmacol. 2014 Sep 15;279(3):455-66. doi: 10.1016/j.taap.2014.06.025. Epub 2014 Jul 11. PubMed PMID: 25019461.

18: Gillette R, Miller-Crews I, Skinner MK, Crews D. Distinct actions of ancestral vinclozolin and juvenile stress on neural gene expression in the male rat. Front Genet. 2015 Mar 2;6:56. doi: 10.3389/fgene.2015.00056. eCollection 2015. PubMed PMID: 25784924; PubMed Central PMCID: PMC4345841.

19: Nakamura A, Takanobu H, Tamura I, Yamamuro M, Iguchi T, Tatarazako N. Verification of responses of Japanese medaka (Oryzias latipes) to anti-androgens, vinclozolin and flutamide, in short-term assays. J Appl Toxicol. 2014 May;34(5):545-53. doi: 10.1002/jat.2934. Epub 2013 Sep 24. PubMed PMID: 24072643.

20: Schneider S, Marxfeld H, Gröters S, Buesen R, van Ravenzwaay B. Vinclozolin--no transgenerational inheritance of anti-androgenic effects after maternal exposure during organogenesis via the intraperitoneal route. Reprod Toxicol. 2013 Jun;37:6-14. doi: 10.1016/j.reprotox.2012.12.003. Epub 2013 Jan 8. PubMed PMID: 23313085.